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Winter Garden, FL 55+ active adult communities & homes for sale

3,958 homes near Winter Garden

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No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 reviews) On Top of the World
<$100k - $600Ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
3.8 rating (14 reviews) Sun City Center
<$100k - $600Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$200Ks - $700Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
3.6 rating (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $300Ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
5 rating (2 reviews) Plantation at Leesburg
$100Ks - $400Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (3 reviews) Stonecrest
$200Ks - $600Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$200Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $900Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$300Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $400Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$400Ks - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $800Ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Spruce Creek North 6180 SW 110TH ST, OCALA, FL, 34476, Ocala, FL 34476
$224,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

6180 SW 110TH ST, OCALA, FL, 34476
Community: Spruce Creek North
Tampa Bay Golf and Country Club 10118 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$420,000

3 beds

|

2 baths

|

1,799 sq ft

|

House

10118 CLEGHORN DR, SAN ANTONIO, FL, 3357...
Trilogy® Orlando 228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$499,000

2 beds

|

2 baths

|

2,197 sq ft

|

House

228 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Alhambra Villas Condominiums 217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724
$244,900

2 beds

|

2 baths

|

1,066 sq ft

|

Condo

217 N HILL AVE 20, DELAND, FL, 32724
Lake James 7929 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$579,000

3 beds

|

2 baths

|

2,653 sq ft

|

House

7929 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 491 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$464,900

2 beds

|

2 baths

|

1,616 sq ft

|

House

491 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Sun City Center 1015 HAREFIELD CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$209,900

2 beds

|

2 baths

|

1,448 sq ft

|

Condo

1015 HAREFIELD CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Trilogy® Orlando 97 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$299,900

2 beds

|

2 baths

|

1,269 sq ft

|

House

97 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
SummerGlen 15680 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$318,457

3 beds

|

2 baths

|

1,917 sq ft

|

House

15680 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Tohoqua Reserve 2749 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$424,030

2 beds

|

2 baths

|

1,943 sq ft

|

House

2749 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Sun City Center 1801 BEDFORD LN APT 46, SUN CITY CENTER,..., Sun City Center, FL 33573
$95,900

1 beds

|

2 baths

|

800 sq ft

|

Condo

1801 BEDFORD LN APT 46, SUN CITY CENTER,...
Community: Sun City Center
Solivita 917 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$494,900

3 beds

|

3 baths

|

2,325 sq ft

|

House

917 SHOREHAVEN DR, POINCIANA, FL, 34759
Community: Solivita
The Villages® 2095 THORNTON TER, THE VILLAGES, FL, 321..., The Villages, FL 32162
$329,900

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2095 THORNTON TER, THE VILLAGES, FL, 321...
Community: The Villages®
Twin Lakes 2460 DREAM HOME CT, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$1,035,900

3 beds

|

2 baths

|

3,146 sq ft

|

House

2460 DREAM HOME CT, SAINT CLOUD, FL, 347...
Community: Twin Lakes
JB Ranch 4691 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$322,165

4 beds

|

2 baths

|

1,828 sq ft

|

House

4691 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15426 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$260,000

2 beds

|

2 baths

|

1,562 sq ft

|

House

15426 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Oak Run 10978 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$220,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

10978 SW 83RD AVE, OCALA, FL, 34481
Community: Oak Run
Quail Meadow 4762 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482
$274,500

2 beds

|

2 baths

|

1,332 sq ft

|

House

4762 NW 30TH PL, OCALA, FL, 34482
Community: Quail Meadow
Twin Lakes 4911 DRAWDY CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$684,000

3 beds

|

2 baths

|

3,122 sq ft

|

House

4911 DRAWDY CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Stonecrest 17243 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$495,000

3 beds

|

2 baths

|

1,729 sq ft

|

House

17243 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Sun City Center 2182 ACADIA GREENS DR # 66, SUN CITY CEN..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2182 ACADIA GREENS DR # 66, SUN CITY CEN...
Community: Sun City Center
Spruce Creek South 17594 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,900

2 beds

|

2 baths

|

1,884 sq ft

|

House

17594 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Latitude Margaritaville 556 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$449,999

2 beds

|

2 baths

|

1,503 sq ft

|

House

556 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
On Top of the World 8920 SW 97TH LANE RD F, OCALA, FL, 34481, Ocala, FL 34481
$169,300

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

8920 SW 97TH LANE RD F, OCALA, FL, 34481
Community: On Top of the World
Lakes of Mount Dora 2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$559,990

3 beds

|

2 baths

|

2,180 sq ft

|

House

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Kings Ridge 3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$339,900

3 beds

|

2 baths

|

1,552 sq ft

|

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Sun City Center 2618 NEWCOMB CT # 12, SUN CITY CENTER, F..., Sun City Center, FL 33573
$189,900

2 beds

|

2 baths

|

963 sq ft

|

Condo

2618 NEWCOMB CT # 12, SUN CITY CENTER, F...
Community: Sun City Center
Lakes of Mount Dora 8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$454,990

3 beds

|

2 baths

|

1,524 sq ft

|

House

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
Ocala Palms 2051 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$254,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

2051 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
Highland Lakes 26913 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

4 beds

|

2 baths

|

2,202 sq ft

|

House

26913 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Sun City Center 2028 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$269,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2028 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
Plantation at Leesburg 24023 ROBINWOOD ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$423,000

3 beds

|

3 baths

|

2,563 sq ft

|

House

24023 ROBINWOOD ST, LEESBURG, FL, 34748
Valencia Lakes 15908 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$329,900

3 beds

|

2 baths

|

1,859 sq ft

|

House

15908 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Stone Creek 9229 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$498,888

3 beds

|

3 baths

|

2,110 sq ft

|

House

9229 SW 52ND PLACE RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 6751 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$288,882

2 beds

|

2 baths

|

1,706 sq ft

|

Villa

6751 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 9223 SW 109TH LN, OCALA, FL, 34481, Ocala, FL 34481
$200,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

9223 SW 109TH LN, OCALA, FL, 34481
Community: Oak Run
Solivita 153 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$259,900

2 beds

|

2 baths

|

1,491 sq ft

|

House

153 VENTANA DR, POINCIANA, FL, 34759
Community: Solivita
Highlands Ridge 5116 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$389,000

2 beds

|

2 baths

|

1,495 sq ft

|

Villa

5116 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
El Dorado 3560 SW 24TH AVENUE RD, OCALA, FL, 34471, Ocala, FL 34471
$599,000

4 beds

|

3 baths

|

2,798 sq ft

|

House

3560 SW 24TH AVENUE RD, OCALA, FL, 34471
Community: El Dorado
Esplanade at Wiregrass Ranch 4257 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$659,000

3 beds

|

2 baths

|

1,934 sq ft

|

House

4257 ROSATTI RD, WESLEY CHAPEL, FL, 3354...

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3,958 homes near Winter Garden
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